data_MEF
# 
_chem_comp.id                                    MEF 
_chem_comp.name                                  "N-({4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl]phenyl}carbonyl)-L-glutamic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H23 N7 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         5,10-methylene,5,6,7,8-tetrahydrofolate 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-12-05 
_chem_comp.pdbx_modified_date                    2008-12-05 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        457.440 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MEF 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3BHR 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
MEF OE2  OE2  O 0 1 N N N 43.954 27.620 44.485 -7.883 2.701  0.413  OE2  MEF 1  
MEF CD   CD   C 0 1 N N N 44.679 26.884 45.155 -7.386 2.066  1.313  CD   MEF 2  
MEF OE1  OE1  O 0 1 N N N 44.297 26.670 46.415 -7.594 2.432  2.588  OE1  MEF 3  
MEF CG   CG   C 0 1 N N N 45.943 26.224 44.597 -6.537 0.860  1.004  CG   MEF 4  
MEF CB   CB   C 0 1 N N N 46.185 26.548 43.107 -6.467 0.660  -0.512 CB   MEF 5  
MEF CA   CA   C 0 1 N N S 46.858 25.403 42.317 -5.606 -0.564 -0.826 CA   MEF 6  
MEF CT   CT   C 0 1 N N N 48.252 25.052 42.782 -5.636 -0.833 -2.308 CT   MEF 7  
MEF O1   O1   O 0 1 N N N 48.582 23.895 43.404 -6.803 -1.092 -2.919 O1   MEF 8  
MEF O2   O2   O 0 1 N N N 49.102 25.901 42.551 -4.610 -0.816 -2.947 O2   MEF 9  
MEF N    N    N 0 1 N N N 46.018 24.226 42.338 -4.226 -0.312 -0.403 N    MEF 10 
MEF C    C    C 0 1 N N N 45.060 24.072 41.422 -3.414 -1.344 -0.102 C    MEF 11 
MEF O    O    O 0 1 N N N 44.805 24.921 40.578 -3.826 -2.486 -0.180 O    MEF 12 
MEF N10  N10  N 0 1 N N N 42.049 19.134 41.518 1.896  -0.373 1.522  N10  MEF 13 
MEF CM   CM   C 0 1 N N N 42.690 18.256 40.509 2.654  0.347  0.466  CM   MEF 14 
MEF N5   N5   N 0 1 N N N 41.987 18.713 39.268 4.056  -0.028 0.631  N5   MEF 15 
MEF C9   C9   C 0 1 N N N 40.595 19.223 41.142 2.650  -1.652 1.678  C9   MEF 16 
MEF C6   C6   C 0 1 N N R 40.554 18.803 39.686 4.112  -1.189 1.554  C6   MEF 17 
MEF C7   C7   C 0 1 N N N 39.883 19.769 38.782 4.976  -2.245 0.857  C7   MEF 18 
MEF N8   N8   N 0 1 N N N 40.259 19.391 37.387 6.266  -1.627 0.510  N8   MEF 19 
MEF C8A  C8A  C 0 1 N N N 41.562 19.295 37.037 6.325  -0.359 -0.043 C8A  MEF 20 
MEF C4A  C4A  C 0 1 N N N 42.481 18.936 38.016 5.211  0.479  0.015  C4A  MEF 21 
MEF N1   N1   N 0 1 N N N 41.949 19.556 35.766 7.440  0.082  -0.636 N1   MEF 22 
MEF C2   C2   C 0 1 N N N 43.250 19.451 35.440 7.502  1.291  -1.152 C2   MEF 23 
MEF NA2  NA2  N 0 1 N N N 43.612 19.698 34.180 8.667  1.701  -1.749 NA2  MEF 24 
MEF N3   N3   N 0 1 N N N 44.182 19.107 36.354 6.444  2.145  -1.111 N3   MEF 25 
MEF C4   C4   C 0 1 N N N 43.837 18.842 37.629 5.284  1.758  -0.532 C4   MEF 26 
MEF O4   O4   O 0 1 N N N 44.728 18.519 38.444 4.323  2.512  -0.491 O4   MEF 27 
MEF C11  C11  C 0 1 Y N N 44.281 22.790 41.428 -2.024 -1.090 0.323  C11  MEF 28 
MEF C12  C12  C 0 1 Y N N 44.810 21.632 42.017 -1.181 -2.160 0.636  C12  MEF 29 
MEF C13  C13  C 0 1 Y N N 44.069 20.469 42.033 0.115  -1.920 1.032  C13  MEF 30 
MEF C16  C16  C 0 1 Y N N 43.021 22.772 40.837 -1.546 0.221  0.408  C16  MEF 31 
MEF C15  C15  C 0 1 Y N N 42.282 21.604 40.853 -0.249 0.454  0.805  C15  MEF 32 
MEF C14  C14  C 0 1 Y N N 42.796 20.449 41.465 0.587  -0.613 1.121  C14  MEF 33 
MEF HOE1 HOE1 H 0 0 N N N 43.493 27.145 46.587 -8.148 3.210  2.736  HOE1 MEF 34 
MEF HG   HG   H 0 1 N N N 46.806 26.587 45.174 -5.532 1.012  1.397  HG   MEF 35 
MEF HGA  HGA  H 0 1 N N N 45.813 25.135 44.682 -6.979 -0.023 1.466  HGA  MEF 36 
MEF HB   HB   H 0 1 N N N 45.210 26.755 42.641 -7.472 0.508  -0.905 HB   MEF 37 
MEF HBA  HBA  H 0 1 N N N 46.870 27.408 43.072 -6.026 1.543  -0.974 HBA  MEF 38 
MEF HA   HA   H 0 1 N N N 46.973 25.779 41.290 -5.996 -1.430 -0.291 HA   MEF 39 
MEF HO1  HO1  H 0 1 N N N 49.512 23.893 43.597 -6.772 -1.258 -3.872 HO1  MEF 40 
MEF HN   HN   H 0 1 N N N 46.155 23.527 43.040 -3.896 0.598  -0.341 HN   MEF 41 
MEF HM   HM   H 0 1 N N N 43.779 18.399 40.455 2.300  0.045  -0.520 HM   MEF 42 
MEF HMA  HMA  H 0 1 N N N 42.597 17.180 40.716 2.536  1.424  0.590  HMA  MEF 43 
MEF H9   H9   H 0 1 N N N 39.982 18.556 41.765 2.465  -2.094 2.657  H9   MEF 44 
MEF H9A  H9A  H 0 1 N N N 40.186 20.232 41.296 2.394  -2.352 0.883  H9A  MEF 45 
MEF H6   H6   H 0 1 N N N 39.980 17.868 39.609 4.520  -0.905 2.524  H6   MEF 46 
MEF H7   H7   H 0 1 N N N 38.792 19.719 38.911 5.141  -3.087 1.529  H7   MEF 47 
MEF H7A  H7A  H 0 1 N N N 40.195 20.799 39.007 4.477  -2.589 -0.049 H7A  MEF 48 
MEF HN8  HN8  H 0 1 N N N 39.863 18.486 37.229 7.088  -2.115 0.672  HN8  MEF 49 
MEF HNA2 HNA2 H 0 0 N N N 44.600 19.584 34.078 9.430  1.103  -1.786 HNA2 MEF 50 
MEF HNAA HNAA H 0 0 N N N 42.986 19.959 33.445 8.728  2.589  -2.134 HNAA MEF 51 
MEF HN3  HN3  H 0 1 N N N 45.142 19.048 36.081 6.521  3.032  -1.496 HN3  MEF 52 
MEF H12  H12  H 0 1 N N N 45.796 21.651 42.457 -1.546 -3.174 0.568  H12  MEF 53 
MEF H13  H13  H 0 1 N N N 44.474 19.576 42.485 0.767  -2.746 1.274  H13  MEF 54 
MEF H16  H16  H 0 1 N N N 42.625 23.662 40.371 -2.194 1.049  0.163  H16  MEF 55 
MEF H15  H15  H 0 1 N N N 41.305 21.579 40.393 0.120  1.467  0.871  H15  MEF 56 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
MEF OE2 CD   DOUB N N 1  
MEF CG  CD   SING N N 2  
MEF CD  OE1  SING N N 3  
MEF OE1 HOE1 SING N N 4  
MEF CB  CG   SING N N 5  
MEF CG  HG   SING N N 6  
MEF CG  HGA  SING N N 7  
MEF CA  CB   SING N N 8  
MEF CB  HB   SING N N 9  
MEF CB  HBA  SING N N 10 
MEF CA  N    SING N N 11 
MEF CA  CT   SING N N 12 
MEF CA  HA   SING N N 13 
MEF O2  CT   DOUB N N 14 
MEF CT  O1   SING N N 15 
MEF O1  HO1  SING N N 16 
MEF C   N    SING N N 17 
MEF N   HN   SING N N 18 
MEF O   C    DOUB N N 19 
MEF C   C11  SING N N 20 
MEF CM  N10  SING N N 21 
MEF C9  N10  SING N N 22 
MEF C14 N10  SING N N 23 
MEF N5  CM   SING N N 24 
MEF CM  HM   SING N N 25 
MEF CM  HMA  SING N N 26 
MEF C4A N5   SING N N 27 
MEF N5  C6   SING N N 28 
MEF C6  C9   SING N N 29 
MEF C9  H9   SING N N 30 
MEF C9  H9A  SING N N 31 
MEF C7  C6   SING N N 32 
MEF C6  H6   SING N N 33 
MEF N8  C7   SING N N 34 
MEF C7  H7   SING N N 35 
MEF C7  H7A  SING N N 36 
MEF C8A N8   SING N N 37 
MEF N8  HN8  SING N N 38 
MEF N1  C8A  SING N N 39 
MEF C8A C4A  DOUB N N 40 
MEF C4  C4A  SING N N 41 
MEF C2  N1   DOUB N N 42 
MEF NA2 C2   SING N N 43 
MEF C2  N3   SING N N 44 
MEF NA2 HNA2 SING N N 45 
MEF NA2 HNAA SING N N 46 
MEF N3  C4   SING N N 47 
MEF N3  HN3  SING N N 48 
MEF C4  O4   DOUB Y N 49 
MEF C16 C11  DOUB Y N 50 
MEF C11 C12  SING N N 51 
MEF C12 C13  DOUB N N 52 
MEF C12 H12  SING Y N 53 
MEF C14 C13  SING Y N 54 
MEF C13 H13  SING N N 55 
MEF C16 C15  SING Y N 56 
MEF C16 H16  SING N N 57 
MEF C15 C14  DOUB N N 58 
MEF C15 H15  SING Y N 59 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
MEF SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)NC(=NC=2NC3)N)C4)CCC(=O)O 
MEF InChI            InChI                1.02b 
InChI=1/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13+/m1/s1/f/h22-23,25,28,32H,21H2 
MEF InChIKey         InChI                1.02b QYNUQALWYRSVHF-FQAOJTBBDH 
MEF SMILES_CANONICAL CACTVS               3.341 NC1=NC2=C(N3CN(C[C@H]3CN2)c4ccc(cc4)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C(=O)N1 
MEF SMILES           CACTVS               3.341 NC1=NC2=C(N3CN(C[CH]3CN2)c4ccc(cc4)C(=O)N[CH](CCC(O)=O)C(O)=O)C(=O)N1 
MEF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)[N@]2C[C@H]3CNC4=C(N3C2)C(=O)NC(=N4)N 
MEF SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)N2CC3CNC4=C(N3C2)C(=O)NC(=N4)N 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
MEF "SYSTEMATIC NAME" ACDLabs              10.04 "N-({4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl]phenyl}carbonyl)-L-glutamic acid"           
MEF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[(6aR,8R)-3-amino-1-oxo-2,5,6,6a,7,9-hexahydroimidazo[3,4-f]pteridin-8-yl]phenyl]carbonylamino]pentanedioic acid" 
# 
